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<h1><a href="https://archiveofourown.org/works/27808096">Too Many Matches</a> by <a class='authorlink' href='https://archiveofourown.org/users/padalelli/pseuds/padalelli'>padalelli</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Boxer!Dean AU, F/M, Implied Smut, much fluff</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-12-01</td></tr>

<tr><td><b>Updated:</b></td><td>2020-12-01</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-10 16:47:13</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>3,279</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27808096</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/padalelli/pseuds/padalelli</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>AU! Where Dean is a boxer.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Dean Winchester/Reader</td></tr>

<tr><td><b>Comments:</b></td><td>1</td></tr>

<tr><td><b>Kudos:</b></td><td>16</td></tr>

</table>

<a name="section0001"><h2>Too Many Matches</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>“Look at Daddy,” you cooed to the little baby on your lap. “Daddy’s gonna win for you tonight, Ben.”<br/>You were babysitting for Dean Winchester, having been previously employed by Lisa Braeden before she died in a car accident about a year ago, leaving Ben with Dean. He had always been a single father; things just hadn’t worked out with Lisa the way he’d hoped. But now he was a full-time single father on top of being a full-time professional athlete. You felt like you owed it to Lisa to make sure Ben was still well taken care of, which you now knew meant sixty hours a week instead of forty. Thank God Dean had a spare bedroom queued up for you to use if and when he got home especially late. <br/>And it looked like it was going to be one of those nights, if the way the match was going was any indication. Ben started wailing, and you noted the time. “Okay, I think you’ve seen enough. Let’s get you to bed, huh, sweetie?” You hoisted the babe on your waist and brought him to his nursery, trying to soothe him. “I know, honey, you’re tired.” You laid him down in his crib, hoping he might surrender to sleep, but he only cried harder. You picked him back up. “Okay, okay, let’s get you some warm milk,” you shushed. After you fed Ben a small fraction of a bottle, he seemed ready to settle down, but still wouldn’t let you release him. “Ugh,” you groaned. “Okay, let’s go sleep in Daddy’s room.” You only ever used it as a last resort method to get the child to sleep. Generally, you just had to lay in Dean’s bed and watch some cartoons for a little bit before Ben fell asleep and you could put him in his crib and retire to the guest room. But tonight you were so exhausted that you accidentally fell asleep right after Ben did. <br/>Dean headed straight to the guest room to wake you up, assuming that was where you were since he didn’t see you in the living room. But the bed hadn’t even been touched yet. “Hm…” Dean humphed before making his way to the nursery, which was also empty. He started to worry when he caught a glance of his bedroom door out of the side of his eye— usually closed, now slightly ajar. He poked his head in and saw your sleeping figure in the middle of the king-sized bed, Ben curled up beside you. Dean quietly stepped over to the bed and gently took Ben in his arms, careful not to wake either of you. After he brought the child back to his crib, he went back into his room, unsure whether he should wake you or not. Given everything you had done for him in the past year, it felt rude for him to bother you and make you move. <i>I’ll figure it out after I take a shower,</i> he told himself. Sure, he had an ice bath after the match, but nothing beat a hot shower before bed. You stirred awake at the sound of a thud in the bathroom. “Shit,” Dean grumbled. <br/><i>Oh shit he’s home and I fell asleep in his bed!</i> You stumbled out of the room and into the living room before Dean could come back out of the bathroom. Once you started collecting your things, you realized you left your phone on the nightstand in Dean’s room. “Shit,” you hissed at yourself. <br/>“Looking for this?” Dean’s voice echoed through the open space. You turned around to see him holding up your phone, clad in a t-shirt and sweatpants. “Listen, I’m sorry I got back so late tonight, the interviews took longer—“ <br/>You interrupted him, knowing it was always the same excuse. “Don’t worry about it. Did you at least win the match?” you asked as you took your phone from his hands.<br/>He looked down and chuckled. “Yeah, you should see the other guy.” He had a couple of bruises on his face, but nothing major. You could tell he had been on his defense tonight. <br/>You laughed awkwardly. “Well, I better head out…” <br/>“You’re welcome to stay in the guest bed tonight. You seem tired…” he offered in a concerned voice. <br/>You shrugged, not wanting to impose any more than you already had. “I’ll be fine.”<br/>He grabbed your wrist, his fatherly side asserting itself. “You know, driving tired is more dangerous than driving drunk…” <br/>“I really shouldn’t impose,” you argued nervously. <br/>He withdrew his hand. “Then I’ll promote you. Live-in nanny. You can use the guest house out back in your off time. I feel bad that you have to be here so much <i>and</i> undoubtedly pay rent for some apartment you barely see.” <br/>His offer took you aback. You weren’t sure what to say because you were so surprised he was being so casual about it. “Um… C-could I think about that for a day or so?” you stuttered out. <br/>It seemed to click in his head then that what he had offered you was actually quite a big adjustment. “Of course, yeah. But only if you stay in the guest room tonight. I can’t condone tired driving.” He tried to be playful. <br/>You rolled your eyes. <i>What a dad.</i> “Fine. But tomorrow is still my day off,” you replied. <br/>As you laid in Dean’s guest bed that night, you thought about his proposition. <i>I bet the guest house is nicer than my apartment anyway,</i> you told yourself. <i>Plus it would be nice to not have to worry about rent or utilities…</i> Dean was definitely right about the fact that you never saw your own place. <i>On the downside… the media would probably be all over it…</i> And you did not want that kind of attention, no matter how small of a blip it made in mainstream sports. You decided you’d talk terms with him in the morning.<br/>When the morning came, you woke up and went into the kitchen to find Dean and Ben. Dean was making breakfast and the boy was seated happily in his highchair. “Mornin’,” Dean greeted you cheerfully. “Pancakes?” <br/>You smiled and took a place at the kitchen island. “I would say no, but I don’t think you boys can take all two dozen of those down by yourselves,” you joked. “Got any fresh berries?” But you already knew the answer. His fridge was always stocked with fresh fruits and veggies. <br/>He chuckled to himself and started prepping a plate for you. “Hey, I didn’t mean to freak you out with that job offer last night,” he said out of the blue. <br/>You looked at him questioningly. “Why would I be freaked out?”<br/>He stopped in his tracks and looked up at you. “You’re considering it?” he asked, shocked. <br/>You shrugged. “It would certainly save me a lot of money. I’m just worried what the press would think,” you admitted. <br/>He resumed filling your plate before sliding it over to you. “I don’t think I would let anything get too out of hands in that department,” he said reassuringly. “People aren’t that interested in a second rate boxer like me.”<br/>“Maybe not, but everyone loves a good nanny scandal,” you joked before digging in. <br/>“Well, good thing there’s nothing scandalous going on here,” he mumbled. <br/>“I should get going,” you said after finishing your meal. “I’ll be back tomorrow.” You practically ran out of the house and out to your car, desperate to escape the embarrassment of the situation you had just put yourself in. “What the fuck is wrong with you?” you hissed at yourself once you were alone. <br/>*<br/>Dean was sitting in the living room watching tv when you came in for work the next morning. “Hey,” he said somewhat softly, getting up to meet you so he wouldn’t be yelling across the room. “Ben’s still sleeping. You had him up pretty late the other night, didn’t you?”<br/>You laughed nervously. “I tried to get him to bed earlier—“ <br/>“I’m kidding. Hey, let me show you the guest house. It occurred to me that you’ve never seen it, given that I never use it.” He tried to joke. <br/>“What if Ben wakes up?” you asked. <br/>“My brother came in last night, he’s in the guest room. They’ll be fine.” He gestured for you to follow him. The guest house was nice given that you were pretty sure it hadn’t been touched in over a year. “I can get it cleaned up, obviously…” Dean said after looking around. <br/>“No, it’s fine, I’ll clean it…” you mumbled, trying to ignore the way his eyes were glued to you. The same way you had ignored your heart racing the other night when he touched you. <br/>“So you’ll do it?” he asked eagerly. <br/>“Let’s do a two week trial period and see how it goes,” you told him. <br/>“At least let me give you a bonus to cover that half month of rent,” he insisted. <br/>You knew that no matter how much you told him you couldn’t accept, he wasn’t going to take no for an answer, so you didn’t try to put up a fight about it. “Fine,” you muttered. <br/>“Well, don’t sound so excited about it,” he teased. <br/>You sighed. “No, I appreciate it, really. You’re a great boss.” You smiled painfully, feeling like you didn’t deserve the luck that threw you into this situation— luck that had been derived from misfortune. <br/>He hesitantly stepped closer to you. “When I made that comment the other night… about scandals… I just meant… It wouldn’t be a scandal… Since neither of us is… involved…” he spoke softly. <br/>You furrowed your brows, not quite processing what he was saying. “What do you mean? What wouldn’t be a scandal?” <i>You becoming a resident caretaker?</i> Before you could even finish your thought, Dean’s lips were pressed against yours. <i>Wait what is he doing?</i> You finally collected your thoughts. “Dean.” You pulled yourself away. “I don’t want to lose this job.” <i>Why did I say that?</i> You chastised yourself. <i>Why did I let him kiss me in the first place?</i> <br/>He instantly put several feet of distance between you, realizing his mistake. “Oh, god, I’m so sorry, I shouldn’t have… It’s not like that, [Y/N], I swear…” <br/>Dean Winchester just invited you to move in and then kissed you. <i>What is happening…</i> you wondered. <br/>“Let me take you out on a date.” His words interrupted your panicked thoughts. <br/>You shook your head, bringing yourself back to reality. “What?” <i>And now he’s asking me out on a date? Am I being punked?</i><br/>“Dinner. Next Saturday. I’ll take you somewhere nice,” he said, as if that was going to help you understand what was going on. <br/>“I-I don’t… You w-wanna… <i>What?</i>” you babbled like an idiot. <br/>“Ben will be with my mom, I wanna take you on a date.” He gradually reapproached you. <br/><i>Dean wants to take me on a nice dinner date…</i> “O-okay,” you stuttered. He grinned and planted another kiss on your cheek before leaving you there, dazed. <br/>*<br/>Thankfully, since you had the guest house now, you didn’t have to see much of Dean leading up to the dinner date. It would’ve been too awkward. Not that figuring out what to wear was going all that great. <i>I guess you can never go wrong with a simple black dress… he did say he wanted to take me somewhere nice…</i> You flipped through a couple of pieces before selecting the dress that seemed to be the perfect combination of classy and sexy. You dressed it up with some red heels when you heard Dean’s knock on the door. “Coming,” you shouted, stumbling over to the door. <br/>Dean took a deep breath when he saw you; he never got to see you in anything but jeans and a t-shirt, and this was <i>damn</i>. “Wow… You look… stunning.” He struggled for words. <br/>You blushed and grabbed your purse off the hook by the door, taking in his appearance as well. He was wearing a perfectly tailored navy suit with a crisp white button-down underneath, foregoing a tie. “You look very handsome yourself,” you replied weakly. <br/>He offered you his arm. “Come on, I got us a reservation.” <br/>He opened the car door for you before climbing in next to you. “You’re not driving?” you asked. <br/>He chuckled. “No, I get concussed so often that my trainer insists on driving me everywhere,” he replied quietly, gesturing to the partition. <br/>You nodded. “So that’s why you don’t condone tired driving,” you teased. <br/>“I guess you could say that,” he snickered. “What kind of music do you prefer?” He took his phone out of his jacket pocket and connected it to the car’s bluetooth.<br/>“I don’t know, rock?” you said the first thing that came to mind, assuming he had seen your various band tees, but you were giving him way too much credit for paying attention to what you wore. “Led Zeppelin…” <br/>He laughed to himself again before selecting a playlist and lowering the volume so you could still have conversation. “You’re awesome,” he mused when he turned back to you. <br/>You giggled, “What?” For some reason you felt butterflies at the idea of him admiring you that way. <br/>“My dream girl loves Led Zeppelin,” he flirted, scooting closer. <br/>You found yourself thinking about how much you wanted to kiss him again. His lips had felt so perfect against yours. “Oh really? Tell me more about this dream girl.” You hoped you sounded more confident than you felt. <br/>“Well, she’s nothing compared to this girl that takes care of my kid. But she does look damn good in that black dress.” You could feel his breath on your skin by the time he finished speaking, and your lips were drawn to his like a magnet, this time sending sparks flying. <br/>You restrained yourself from becoming too caught up in it and doing things you definitely should not be doing in the back of a car before you even had dinner yet. “Wow,” you said breathlessly when you could finally pull yourself away. <br/>“Yeah… wow…” he murmured. <br/>You scooted away slightly and laughed nervously. “Um…” you struggled to figure out what to say next. “Why did you ask me out?” <br/>He shrugged and gazed at you. “I’ve had this silly crush on you ever since Lisa hired you. I thought it was too cliche, but now…” he trailed off.<br/>“Now what?” <br/>He shook his head. “I’ll tell you later.”<br/>“No, tell me now,” you whined. <br/>“It wouldn’t be in my best interest,” he teased. <br/>“Fine, then you can take me right home,” you threatened unconvincingly. <br/>Dean sighed and gave in. “I can’t keep denying the way I’ve been feeling about you,” he admitted. <br/>“Oh?” you replied, intrigued. <br/>“I really shouldn’t embarrass myself more than I already have.” <br/>“I don’t know why you’re embarrassed… I guess I can say I know how you feel…” you revealed. <br/>*<br/>Your date with Dean flew by, and before you knew it, the bartender was letting you know it was last call. You looked around, realizing the restaurant was mostly empty. “Oh wow, my apologies,” Dean told the host when he checked the time. He walked you slowly back to the car so he could have more time with you. “Well, I hope you enjoyed yourself…” <br/>You gazed up at him, falling deeper into his eyes with every glance. “I did. Very much… I’m just worried it will make things with my boss… awkward…” You tried to be nonchalant. <br/>“Maybe it would be less awkward if you stopped calling him your boss.”<br/>You sneered. “Okay, then what should I call him?” <br/>He thought for a moment before capturing your face in his hands. “He would probably prefer ‘man of your dreams’. But I’m sure he’d settle for boyfriend, too.” Then he was kissing you again, and it felt so wrong but so right. <br/>You pulled back for air and tried to collect your thoughts. “Dean, I really shouldn’t…” Despite the fact that every bone in your body was telling you to be with him. <br/>“Have you not been paying attention to a single word I’ve been saying all night?” he chastised. <br/>The answer was yes, you had, but it still didn’t seem quite real that the man you had been pining over for the last few months actually wanted you too. “But what if—“ <br/>He interrupted you, knowing where your thought was headed. “I don’t think that’s going to be an issue.” He opened the car door. “Come on, I’ll take you back.”<br/>“Where exactly back to?” you asked as you climbed into the backseat. <br/>“I mean, if you’d like to go to your apartment, I can have us-you dropped off there.” You noticed his quick self-correction, but decided to ignore it. <br/>“Hm… Don’t you have the house to yourself tonight?” you remembered. You’d never thought about his house without Ben inside of it. <br/>Dean smiled at your suggestion once he got in the car. “I do,” he said matter-of-factly, closing the door. <br/>“Well, it is nicer there,” you told him. He had never been to your shitty apartment and you certainly didn’t want him to start now. Especially not if it would ruin your chances of getting a second date with Dean Winchester. <br/>“Then off we go.” He took your hand and angled himself towards you. <br/>“Dean, can I ask you something?” you inquired nervously. <br/>“Anything. I’ve been asking you questions all night,” he replied. <br/>“Why are you interested in me? And don’t say anything about Ben.” <br/>He scoffed. “Okay. Well, for starters, you’re beautiful. You’re kind, you’re smart—“<br/>“But isn’t that what everyone says about the people they’re interested in? Come on, be more specific.”<br/>He sighed exasperatedly. “Fine… you have great taste in music… food, too, I’ve recently discovered… You always offer people things, you don’t like to take other people’s offers… You’re shy until you get to know people, it’s pretty cute actually…”<br/>“Okay, okay. Point made,” you giggled. “And you’re sure enough about me that you’re willing to lose me as a nanny?” <br/>“I don’t see it as losing anything.” He lowered his voice to a whisper. “I want you to be more than just that… But what I really hope is that you feel the same…” <br/>You couldn’t figure out what words would be best, so you just nodded enthusiastically until you did. “I-I do…” you stammered. “I just… I never thought you’d feel the same way… We never spent much time together…” <br/>Dean nodded. “I know. And that’s my fault. Once I get past the next few weeks, things are going to slow down, I promise.” He squeezed your hand. <br/>You were on him as soon as he closed the front door, arms wrapped tightly around him as you pressed your lips to his. “Dean, I don’t wanna be shy anymore,” you breathed. <br/>“Then don’t,” he replied quickly before picking you up and carrying you to his room. <br/>*<br/>You were vaguely aware of where you were when you woke up in the morning, but still had to remind yourself that you spent the night with Dean… Hopefully you could continue to. As soon as you began to stir, so did he. “Good morning,” he said happily, cuddling up to you. <br/>“No alarm? Nothing on the agenda today?” you asked groggily. <br/>Dean shook his head. “Nope.” He popped the ‘p’. “Gives us a whole day to spend together. What do you wanna do?”<br/>You giggled, gazing into his mossy eyes. “Honestly? You some more.”</p>
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